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US 8,785,594 B2Granted
Glycoproteins and glycosylated cells and a method for the preparation of the same
AssigneeGlycom A/S
InventorsGyula Dekany, Károly Ágoston, István Bajza, Marie Bøjstrup, Lars Kröger
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Abstract
The present application discloses novel glycoproteins and a related glycosylcarbamoylation methodology suitable for the preparation of glycopeptides (in particular glycoproteins and glycosylated cells), as well as the use of such glycoproteins in medicine, e.g. as pharmaceuticals and diagnostics or in diagnostic kits. A method for the preparation of a carbohydrate-peptide conjugate includes reacting a cyclic carbamate with a peptide which has at least one primary amino group.
Claims19
A method for the preparation of a carbohydrate-peptide conjugate, said method comprising:
- reacting a cyclic carbamate (1) with a peptide,
- wherein R3 and R4 are independently selected from the group consisting of hydroxyl, acetamido, and a carbohydrate moiety,
- R5 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acetamidomethyl, carboxyl, and X—(CH2)r—, wherein X is a carbohydrate moiety and r is an integer selected from 0, 1, 2 and 3, and
- said peptide includes at least one primary amino group, and said peptide is a cell surface or cell membrane bound protein,
- and said carbohydrate-peptide conjugate includes at least one moiety selected from the group consisting of General Formulae 1 and 2
- wherein, in General Formula 1,
- R1 and R2 together with the intervening lysine moiety represent a cell surface or cell membrane bound protein;
- R3, R4 and R5 are as defined at cyclic carbamate (1), and pharmaceutically acceptable salts thereof,
- and
- wherein, in General Formula 2,
- R11 is an amino acid side chain;
- R12 together with —NH—CHR11—C(═O)— represents a cell surface or cell membrane bound protein,
- R3, R4 and R5 are as defined at cyclic carbamate (1), and pharmaceutically acceptable salts thereof.
10 more elements
A carbohydrate-peptide conjugate, comprising:
- at least one moiety of General Formula 1:
- wherein,
- R1 and R2 together with the intervening lysine moiety represent a cell surface or cell membrane bound protein;
- R3 and R4 are independently selected from the group consisting of hydroxyl, acetamido, and a carbohydrate moiety,
- R5 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acetamidomethyl, carboxyl, and X—(CH2)r-, wherein X is a carbohydrate moiety and r is an integer selected from 0, 1, 2 and 3 and
- pharmaceutically acceptable salts thereof.
3 more elements
A carbohydrate-peptide conjugate, comprising:
- at least one moiety of the General Formula 2:
- wherein
- R11 is an amino acid side chain;
- R12 together with —NH—CHR11—C(═O)— represents a cell surface or cell membrane bound protein,
- R3 and R4 are independently selected from the group consisting of hydroxyl, acetamido, and a carbohydrate moiety,
- R5 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acetamidomethyl, carboxyl, and X—(CH2)r-, wherein X is a carbohydrate moiety and r is an integer selected from 0, 1, 2 and 3, and
- pharmaceutically acceptable salts thereof.
4 more elements
A cyclic carbamate of an oligosaccharide selected from (4a), (4b) and (4c)
- wherein the cyclic carbamate excludes (4-O-β-D-glucopyranosyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-d]oxazolidine-2-one and (4-O-β-D-galactopyranosyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-d]oxazolidine-2-one;
- and
- R3, R4, R6 and R7 are independently selected from the group consisting of hydroxyl, acetamido, and a carbohydrate moiety;
- R5 and R9 are independently selected from the group consisting of hydrogen, methyl, hydroxymethyl, acetamidomethyl, carboxyl, and X—(CH2)r-, wherein X is a carbohydrate moiety and r is an integer selected from 0, 1, 2 and 3;
- and
- R8 and R10 are independently selected from the group consisting of hydroxyl, C1-6-alkoxy, C1-6-acyloxy, acetamido, and a carbohydrate moiety;
- and
- pharmaceutically acceptable salts thereof.
5 more elements
A carbohydrate-peptide conjugate selected from the group consisting of General Formulae 1 and 2:
- wherein, in General Formula 1,
- R1 and R2 together with the intervening lysine moiety represent a cell surface or cell membrane bound protein;
- R3 and R4 are independently selected from the group consisting of hydroxyl, acetamido, and a carbohydrate moiety,
- R5 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acetamidomethyl, carboxyl, and X—(CH2)r—, wherein X is a carbohydrate moiety and r is an integer selected from 0, 1, 2 and 3, and pharmaceutically acceptable salts thereof,
- and General Formula 2:
- wherein, in General Formula 2,
- R11 is an amino acid side chain;
- R12 together with —NH—CHR11—C(═O)— represents a cell surface or cell membrane bound protein,
- R3 and R4 are independently selected from the group consisting of hydroxyl, acetamido, and a carbohydrate moiety,
- R5 is selected from the group consisting of hydrogen, methyl, hydroxymethyl, acetamidomethyl, carboxyl, and X—(CH2)r—, wherein X is a carbohydrate moiety and
- r is an integer selected from 0, 1, 2 and 3, and pharmaceutically acceptable salts thereof.
8 more elements
Dependencies are inferred from the claim text.